In a large bowl, mix together the pudding, pumpkin, pumpkin pie spice, and vanilla. Gently stir in the cool whip. This will take about 5 minutes to get a smooth texture.
Add dip to the hollowed pumpkin and serve with fruit and Cinnamon Sugar Tortilla Cutouts.
To Make the Cinnamon Tortilla Cutouts:
Preheat oven to 350°F.
Use cookie cutters or cut tortillas into desired shapes. Place them on a lined baking sheet.
Spray tortillas with butter flavored spray and sprinkle with cinnamon sugar as desired. Spray again to make sure the cinnamon sugar adheres.